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1542741180
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note
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Treatment of 5-bromovaleronitrile with n-propylmagnesium chloride provided a mixture that was 52% 5a by GC analysis (uncorrected for response factors). Reaction of n-undecylmagnesium bromide with the same bromonitrile gave a mixture that contained only 5% 5b by GC analysis.
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30
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1542741179
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note
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By employing benzene as a cosolvent during the Grignard reaction and performing the imine hydrolysis at 60°C instead of room temperature, we have been able to prepare the related 2-ethyl-3,4,5,6-tetrahydropyridine without isolation of the intermediate chloroketone in 67% overall yield after distillation: Yang, B. H.; Buchwald, S. L. Unpublished results. See also ref 10.
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85086527704
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note
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1H NMR) identical to previously prepared samples.
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